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S. A. Yamashkin, O. V. Pozdnyakova, M. A. Yurovskaya
Synthesis of pyrrolo[3,2-f]quinolines via
reaction of 2,5-dimethyl- or, 1,2,5-trimethyl-6-aminoindoles with β-ketoesters
Abstract
Reaction of 2,5-dimethyl- or
1,2,5-trimethyl-6-aminoindoles with ß-ketoesters (methyl and ethyl
acetoacetates, diethyl oxaloacetate) was found to proceed chemoselectively via
interaction between amino group of indole and carbonyl function of ketoether leading
to enamines formation. In contrast to enamines, synthesized from similar
aminoindoles and β-diketones, enamines from β-ketoesters can easily undergo thermal cyclization furnishing
pyrrolo[3,2-f]quinolines with angular catenation of rings.
Key words: 6-amino-2,5-dimethylindole,
6-amino-1,2,5-trimethylindole, methyl acetoacetate, ethyl acetoacetate, diethyl
oxaloacetate, pyrrolo[3,2-f]quinolines.
Copyright (C) Chemistry Dept., Moscow State University, 2002
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